Kimberly Blessing has run the gamut of roles in the computing/IT industry, from software sales and tech support to Web strategist and tech manager. She is also one of the fine people who has volunteered to mentor aspiring speakers over at Make Me A Speaker!. I asked her some questions over email:

KB: My first Web conference-speaking gig was in 2004 at SXSW Interactive. I was working for AOL at the time and had recently joined the W3C CSS Working Group on their behalf; there I got to know Tantek Çelik, who was a member on behalf of Microsoft. He was organizing a panel entitled “CSS: The Good, The Bad, and The Ugly” and asked me to be part of it. I spoke for about 7 minutes, showing the cool CSS-driven “super layout” system I had helped to create for AOL.

However, prior to that event, I had done plenty of public speaking. At AOL, I had given presentations on a variety of topics to senior-level execs; when I worked in tech support, I conducted training sessions for both technical staff and non-technical users; in college, I was a TA for Computer Science classes. Talking “tech” in front of an audience was far from new to me.

MW: What do you think the most important thing is for someone who wants to be a successful speaker?

I think there are two things that are equally important:

First, you must be confident in yourself. This doesn’t mean that you have to believe that you know everything or think that you are perfect! In fact, it means, in part, that you’re willing to admit what you don’t know. The other part means being comfortable with any “quirks” you may have and not feeling self-conscious when you’re in front of an audience and those quirks come out.

For example, I have a slight lisp, and when saying things like “CSS” a lot, I sound silly. I used to think that I didn’t sound professional, but then a good friend (a voice-over artist) pointed out that I dramatically lowered my voice when pronouncing words that would make my lisp known. It was then that I realized that I’d rather have someone hear my lisp than not be able to hear me at all! The next time I gave a talk about CSS, I recorded myself to make sure I maintained volume throughout, and I asked a few people for feedback on my enunciation — one person hadn’t noticed my lisp at all, and others said it was barely noticeable. So now, I just don’t worry about it.

Second, you have to practice! You cannot expect to be a great speaker the very first time you deliver a talk if you haven’t rehearsed it ahead of time. Once you’ve determined your message, outlined what you want to say, and generated some of the content or examples, you need to start talking, even if it’s to yourself! I will even record myself while ideating, which I do aloud; this allows me to listen for powerful phrasing or succinct wording that I would easily forget if trying to talk and type or write.

As soon as I get to the point where I hear myself repeating the same phrases repeatedly, I start rehearsing in front of others. I do this to make sure that if I’m not being clear with my statements, someone informs and corrects me before those statements “take root” in my head and come out later. I typically rehearse with a peer group that is already familiar with my message first, so that they can poke holes in my line of thought. Then I move on to rehearsing with those that aren’t as familiar with my topic or message. In cases like that, I also present to my husband, who has just enough tech/Web knowledge to be dangerous; he’s great not only for ensuring my message gets understood, but he also helps me work through those quirks I referred to earlier.

By the way, I also tell people who ask that these are the most important things when it comes to job interviewing as well.

For me, the hardest part is coming up with a “worthy” topic. At work, my speaking topics are nearly all driven by organizational need, so there I spend my creative energies on the content and message. However, when it comes to formulating an idea to pitch to conference organizers, I often find myself struggling.

To solve this problem, I try to look at conferences like I do my work. I will ask the conference organizers about their wants or needs, or those of their audience, and I will look to craft a topic idea that fits. I also find that talking to friends in the industry can help spark ideas, and finding someone to co-craft a proposal makes things easier.

JK : The first time I spoke in front of a crowd was at a local gathering here in Brighton called Silicon Beach. A bunch of web geeks would get together in the pub and one person would display their work and talk about it. This was a few year’s ago before CSS had really caught on so I was in full evangelising mode.

After that, I spoke at another local event was Skillswap, organised by Andy Budd. Again, it was a small gathering with a bunch of peers and again, I was flying the CSS flag high. I think the fact that I was speaking about something I cared passionately about made all the difference. If I spoke on that subject now, I probably wouldn’t be as good; I’m a bit more jaded about CSS now and I probably wouldn’t be able to muster up the same youthful enthusiasm.

Speaking at those small local events gave me (and Andy) the courage to submit a proposal for South by Southwest in 2005, which was my first proper conference slot.

MW : What do you think the most important thing is for someone who wants to be a successful speaker?

JK : Passion. If there’s something you care strongly about, chances are you will deliver an awesome presentation on that subject. Sure, there are plenty of tips’n’tricks about body language and slideshow software to help you deliver the presentation, but if you have a subject that you really care strongly about, I think you’re 90% of the way to knocking an audience’s socks off.

JK : Self-confidence. I honestly think that that’s the thing that holds back a lot of first-time speakers. Most conference organisers are quite eager to get new blood, in my experience. It’s the new blood that’s often too timid about presenting themselves. Still, having something to point to show that you can back up your claims really
helps — a blog is probably the best way of showing how committed and passionate you are.

JA: Well, I did debating at school, and all kinds of post secondary and adult teaching, particularly after finishing university – that certainly would have helped my confidence in front of audiences, and through teaching, I knew I loved helping people learn.

In terms of speaking at conferences and so on, probably the first presentation I can recall was actually at the Parsons School of Design, at the New School University in New York City. It’s now famous as the location for Project Runway, but they’ve had brilliant design courses there for a long time.

I happened to spend a couple of months in New York back in 2000, and connected up with some folks whom I started emailing with after my article “A Dao of Web Design” was published at A List Apart. One of them did some teaching at Parsons, and they had an open day, and asked whether I’d do a guest lecture. Which I very proudly did. I am pretty sure I sucked. I hope I suck less now.

MW: What do you think the most important thing is for someone who wants to be a successful speaker?

JA: In Blink, the reasonably recent book by Malcolm Gladwell, he talks about some research which demonstrates that how good a teacher a class thinks someone is is decided in literally moments, and even without hearing someone speak. If you show very short soundless clips of teacher to a group of people, their opinion of that teachers ability is pretty much the same even after a semester of having them as a teacher.

The lesson for me in that is that, well derr, first impressions count. Confident, engaging, warm, human speakers gain people’s trust, and so will have more open, more forgiving audiences.

To me, developing your own natural voice – being true to your personality, while developing confidence, these would be the most important things to develop as a speaker. While some people seem to have these “naturally”, they can certainly be developed and improved.

JA: Like your first job, getting a platform. But it is much easier now than it once was, with so many more events, barcamps, and the like. But there are other avenues as well – developing an audience through writing online – articles, blog posts and so on. Start a podcast, go to events with a recorder and interview people, (probably best tee it up with organizers first, but almost all will be right as rain with that – hey if you are in Australia email me, we’d love to have you do that at our events).

In order to keep the momentum going, I had the idea of doing some email interviews with those who had signed up as potential mentors. Obviously a wiki (which anyone can edit) didn’t seem like the best format for that kind of content, hence the birth of this blog.

So if you’re interested in interviews with established speakers and testimonials from those up-and-coming aspiring speakers as they get more and more experience, subscribe to the feed or just keep visiting 🙂